Dichloromethane → 3-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoroacetylpyrazole

HRID 1387710ノート

反応式

HRID 1387710 の反応式
N(OC(C)(C)C)=O.N[C:9]1[N:13]([C:14]2[C:19]([Cl:20])=[CH:18][C:17]([C:21]([F:24])([F:23])[F:22])=[CH:16][C:15]=2[Cl:25])[N:12]=[C:11]([C:26]#[N:27])[C:10]=1[C:28](=[O:33])[C:29]([F:32])([F:31])[F:30].CCCCCC.ClCCl>O1CCCC1>[C:26]([C:11]1[C:10]([C:28](=[O:33])[C:29]([F:30])([F:31])[F:32])=[CH:9][N:13]([C:14]2[C:19]([Cl:20])=[CH:18][C:17]([C:21]([F:24])([F:22])[F:23])=[CH:16][C:15]=2[Cl:25])[N:12]=1)#[N:27]

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 8058HexaneHCID 10906Tert-Butyl nitrite2 回HCID 186994595-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoroacetylpyrazole

生成物 1

HCID 186994613-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoroacetylpyrazole

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
55 °C

実験手順

t-Butyl nitrite (12.45 ml) was added dropwise to a stirred solution of 5- amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoroacetylpyrazole (JP-A-8-311036; 30 g) in tetrahydrofuran (250 ml) and the mixture stirred at 55° C. for 16 hours. Further quantities of t-butyl nitrite added/subsequent periods of stirring at 55° C. were as follows: 9 ml/7 hours, 6 ml/16 hours, 9 ml/6 hours, 4.75 ml/16 hours, 6 ml/6 hours and 3.5 ml/22 hours. The reaction mixture was allowed to cool and evaporated under reduced pressure, then the residue combined with those obtained from three identical preparations. Purification by column chromatography on silica gel (1 Kg), using hexane:dichloromethane (6:4) and then dichloromethane as eluants, gave a yellow oil which, on trituration with hexane (3×50 ml) followed by dichloromethane (100 ml), provided the title compound as a white solid, m.p. 124-125° C. δ(CDCl3): 7.83 (s,2H), 8.30 (s,1H). MS (thermospray): M/Z [M+H] 401.7; C13H3Cl2F6N3O+H requires 401.96.

後処理

  1. custom9 ml/7 hours, 6 ml/16 hours, 9 ml/6 hours, 4.75 ml/16 hours, 6 ml/6 hours and 3.5 ml/22 hours
  2. temperatureto cool
  3. customevaporated under reduced pressure
  4. customthose obtained from three identical preparations
  5. customPurification by column chromatography on silica gel (1 Kg)
  6. customdichloromethane as eluants, gave a yellow oil which

出典と根拠

ORDレコード
ord-85dc45cbcdf348e0bee48feae88d21d3
出典データセット
uspto-grants-2001_07
特許番号
US06268509B1

反応ノート

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